IE45096B1 - Compositions containing thiadiazole derivatives - Google Patents

Compositions containing thiadiazole derivatives

Info

Publication number: IE45096B1
Authority: IE; Ireland
Prior art keywords: hydrogen; methyl; formula; hydrazino; compound
Prior art date: 1976-06-17

Application number

IE1236/77A

Other languages

English (en)

Other versions

IE45096L (en

Original Assignee

Reckitt & Colmann Prod Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-17

Filing date

1977-06-16

Publication date

1982-06-16

1977-06-16 Application filed by Reckitt & Colmann Prod Ltd filed Critical Reckitt & Colmann Prod Ltd

1977-12-17 Publication of IE45096L publication Critical patent/IE45096L/xx

1982-06-16 Publication of IE45096B1 publication Critical patent/IE45096B1/en

Links

239000000203 mixture Substances 0.000 title claims description 36
150000004867 thiadiazoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 43
239000003085 diluting agent Substances 0.000 claims abstract description 5
238000007911 parenteral administration Methods 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
-1 chloro , bromo , iodo Chemical group 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 14
230000001225 therapeutic effect Effects 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000002552 dosage form Substances 0.000 claims description 5
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
ZUZCTTFDIVHRKT-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound S1C(NN)=NN=C1C1=C(Cl)C=CC=C1Cl ZUZCTTFDIVHRKT-UHFFFAOYSA-N 0.000 claims description 2
125000005055 alkyl alkoxy group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
ZPJMGRXYYGUUSW-UHFFFAOYSA-N [5-(2-propoxyphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CCCOC1=CC=CC=C1C1=NN=C(NN)S1 ZPJMGRXYYGUUSW-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 9
230000036772 blood pressure Effects 0.000 abstract description 4
239000008194 pharmaceutical composition Substances 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000003826 tablet Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000008101 lactose Substances 0.000 description 4
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
LHNKBXRFNPMIBR-UHFFFAOYSA-N Picrotoxin Natural products CC(C)(O)C1(O)C2OC(=O)C1C3(O)C4OC4C5C(=O)OC2C35C LHNKBXRFNPMIBR-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
230000001773 anti-convulsant effect Effects 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000001961 anticonvulsive agent Substances 0.000 description 3
229960003965 antiepileptics Drugs 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
230000001631 hypertensive effect Effects 0.000 description 3
229960005152 pentetrazol Drugs 0.000 description 3
VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 3
238000012216 screening Methods 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
HBDFBWGGWNLMBS-UHFFFAOYSA-N 1,3,4-thiadiazole;hydrochloride Chemical compound Cl.C1=NN=CS1 HBDFBWGGWNLMBS-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
241001279009 Strychnos toxifera Species 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229960005453 strychnine Drugs 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
GNCDLUWRARJVPW-UHFFFAOYSA-N 2-chloro-5-(2-methylphenyl)-1,3,4-thiadiazole Chemical compound CC1=CC=CC=C1C1=NN=C(Cl)S1 GNCDLUWRARJVPW-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
101100297842 Schizosaccharomyces pombe (strain 972 / ATCC 24843) plo1 gene Proteins 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
241000906446 Theraps Species 0.000 description 1
241000534944 Thia Species 0.000 description 1
CQGCSFMILDVJCU-UHFFFAOYSA-N [5-(2,3-dimethylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CC1=CC=CC(C=2SC(NN)=NN=2)=C1C CQGCSFMILDVJCU-UHFFFAOYSA-N 0.000 description 1
DNWZNNBCFVHEKV-UHFFFAOYSA-N [5-(2,3-dimethylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine;hydrochloride Chemical compound Cl.CC1=CC=CC(C=2SC(NN)=NN=2)=C1C DNWZNNBCFVHEKV-UHFFFAOYSA-N 0.000 description 1
HIJZFUAFFSQCEU-UHFFFAOYSA-N [5-(2,4-dimethylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CC1=CC(C)=CC=C1C1=NN=C(NN)S1 HIJZFUAFFSQCEU-UHFFFAOYSA-N 0.000 description 1
YMDOYBBCIKARHA-UHFFFAOYSA-N [5-(2,5-dimethylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine;hydrochloride Chemical compound Cl.CC1=CC=C(C)C(C=2SC(NN)=NN=2)=C1 YMDOYBBCIKARHA-UHFFFAOYSA-N 0.000 description 1
WUBBWGTWOAJIIN-UHFFFAOYSA-N [5-(2-ethylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CCC1=CC=CC=C1C1=NN=C(NN)S1 WUBBWGTWOAJIIN-UHFFFAOYSA-N 0.000 description 1
WPEWNRKLKLNLSO-UHFFFAOYSA-N [5-(2-propoxyphenyl)-1,3,4-thiadiazol-2-yl]hydrazine;hydrochloride Chemical compound Cl.CCCOC1=CC=CC=C1C1=NN=C(NN)S1 WPEWNRKLKLNLSO-UHFFFAOYSA-N 0.000 description 1
INCWXQMAXCKLCL-UHFFFAOYSA-N [5-(2-propylsulfinylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CCCS(=O)C1=CC=CC=C1C1=NN=C(NN)S1 INCWXQMAXCKLCL-UHFFFAOYSA-N 0.000 description 1
LBLHDZZAKNWHAL-UHFFFAOYSA-N [5-(2-tert-butylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CC(C)(C)C1=CC=CC=C1C1=NN=C(NN)S1 LBLHDZZAKNWHAL-UHFFFAOYSA-N 0.000 description 1
WMYBIZIQBFCJHG-UHFFFAOYSA-N [5-(4-fluoro-2-methylphenyl)-1,3,4-thiadiazol-2-yl]hydrazine Chemical compound CC1=CC(F)=CC=C1C1=NN=C(NN)S1 WMYBIZIQBFCJHG-UHFFFAOYSA-N 0.000 description 1
HZODFNKGGIMZAM-UHFFFAOYSA-N [5-[2-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]hydrazine;hydrochloride Chemical compound Cl.S1C(NN)=NN=C1C1=CC=CC=C1C(F)(F)F HZODFNKGGIMZAM-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
230000007775 late Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

IE1236/77A 1976-06-17 1977-06-16 Compositions containing thiadiazole derivatives IE45096B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB25079/76A GB1578135A (en)	1976-06-17	1976-06-17	Compositions containing thiadiazole derivatives

Publications (2)

Publication Number	Publication Date
IE45096L IE45096L (en)	1977-12-17
IE45096B1 true IE45096B1 (en)	1982-06-16

Family

ID=10221870

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1236/77A IE45096B1 (en)	1976-06-17	1977-06-16	Compositions containing thiadiazole derivatives

Country Status (11)

Country	Link
US (1)	US4147794A (fr)
JP (1)	JPS533531A (fr)
AU (1)	AU514177B2 (fr)
BE (1)	BE855846A (fr)
DE (1)	DE2727146A1 (fr)
FR (1)	FR2354767A1 (fr)
GB (1)	GB1578135A (fr)
IE (1)	IE45096B1 (fr)
NL (1)	NL7706689A (fr)
NZ (1)	NZ184331A (fr)
ZA (1)	ZA773462B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8625774D0 (en) *	1986-10-28	1986-12-03	Reckitt & Colmann Prod Ltd	Thiadiazole derivative
GB8709734D0 (en) *	1987-04-24	1987-05-28	Reckitt & Colmann Prod Ltd	Thiadiazole derivatives
DE10052590A1 (de) *	2000-10-24	2002-05-02	Haarmann & Reimer Gmbh	Verwendung von 2-Hydrazino-1,3-thiazolen als Antioxidantien
US20240276957A1 (en) *	2019-06-07	2024-08-22	Agios Pharmaceuticals, Inc.	Methods of treatment with aminolevulinic acid synthase 2 (alas2) modulators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3849567A (en) *	1970-04-27	1974-11-19	Mobil Oil Corp	Use of thiadiazole hydrazones as bactericides

1976
- 1976-06-17 GB GB25079/76A patent/GB1578135A/en not_active Expired
1977
- 1977-06-07 AU AU25910/77A patent/AU514177B2/en not_active Expired
- 1977-06-08 ZA ZA00773462A patent/ZA773462B/xx unknown
- 1977-06-08 US US05/804,728 patent/US4147794A/en not_active Expired - Lifetime
- 1977-06-08 NZ NZ184331A patent/NZ184331A/xx unknown
- 1977-06-16 IE IE1236/77A patent/IE45096B1/en unknown
- 1977-06-16 FR FR7718572A patent/FR2354767A1/fr active Granted
- 1977-06-16 DE DE19772727146 patent/DE2727146A1/de not_active Withdrawn
- 1977-06-17 BE BE6046058A patent/BE855846A/fr not_active IP Right Cessation
- 1977-06-17 JP JP7194877A patent/JPS533531A/ja active Pending
- 1977-06-17 NL NL7706689A patent/NL7706689A/xx unknown

Also Published As

Publication number	Publication date
ZA773462B (en)	1978-07-26
IE45096L (en)	1977-12-17
DE2727146A1 (de)	1978-01-05
JPS533531A (en)	1978-01-13
AU514177B2 (en)	1981-01-29
FR2354767A1 (fr)	1978-01-13
FR2354767B1 (fr)	1983-10-14
NL7706689A (nl)	1977-12-20
US4147794A (en)	1979-04-03
GB1578135A (en)	1980-11-05
NZ184331A (en)	1979-06-08
AU2591077A (en)	1978-12-14
BE855846A (fr)	1977-10-17

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AU751139B2 (en)	2002-08-08	Amide derivative
JPH054983A (ja)	1993-01-14	イソキノリノン誘導体、その製造方法およびその誘導体を有効成分として含有する５−ｈｔ３レセプター拮抗剤
WO2001081345A1 (fr)	2001-11-01	Composes d'amides aromatiques
GB2097387A (en)	1982-11-03	3,4-dihydro-5h-2,3-benzodiazepine derivatives
JPS591712B2 (ja)	1984-01-13	１−（２−チエニルスルホニル）ベンゾイミダゾ−ル化合物
SK18932000A3 (sk)	2001-06-11	Derivát arylalkanoylpyridazínu, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje
RU2193554C2 (ru)	2002-11-27	Производные ароматических аминов, обладающих подавляющим оас действием, способ их получения и ингибитор ноас
GB1588096A (en)	1981-04-15	Pyrrole derivatives
KR860001602B1 (ko)	1986-10-13	피리딘 유도체의 제조방법
NZ206957A (en)	1987-06-30	4-cyano-pyridazines; intemediates and pharmaceutical compositions
IE45096B1 (en)	1982-06-16	Compositions containing thiadiazole derivatives
EP1551828A1 (fr)	2005-07-13	Derives de pyrazole
NZ204369A (en)	1986-09-10	Piperazine derivatives,their production,and pharmaceutical compositions which contain them
CA1246065A (fr)	1988-12-06	5-(3,4-dihydrocarbostyril-6-yl)-3,6-dihydro-1,2,4- thiadiazin-2-one
US4588725A (en)	1986-05-13	2-piperazinyl-quinazoline derivatives and pharmaceutical compositions containing them
CA2881997A1 (fr)	2014-02-20	Tri(hetero)arylpyrazoles et leur utilisation
US3420823A (en)	1969-01-07	Dibenzothiazines
JPH06501690A (ja)	1994-02-24	抗ウイルス薬としてのチアゾロイソインドリノン誘導体の使用
JPH03169862A (ja)	1991-07-23	新規ピリジン誘導体、それらを含む製薬組成物、およびその製造方法
EP0038298B1 (fr)	1984-07-25	Isoxazolylindol-amines
US4399137A (en)	1983-08-16	6-Imidazol-1-yl-3-hydrazino-pyridazines, their preparation and antihypertensive use
US3994920A (en)	1976-11-30	5H-imidazo[2,1-a]isoindol-5-one compounds
US4207317A (en)	1980-06-10	1-Aryl-4-carbamoyl-pyrazolin-5-ones
HU184791B (en)	1984-10-29	Process for preparing derivatives of tetrahydro-pyrid-4-yl-indole
EP0078546B1 (fr)	1986-11-12	Dérivés d'imidazolecarboxamide